5 Things D&D Taught me about Starting a Business

If you’re one of my (very happy!) customers, it’s only a matter of time until I out myself as an enthusiastic nerd to you. My regular ascents up to the realm of imagination bring joy and connection into my life, and I’m eager to share my passions. And Dungeons and Dragons is one of said passions. Now that I’m starting up my own home services business, I find I have a lot to thank the infinite game for. 

There is more to it than laughs. For two years now, I’ve looked forward to my biweekly volunteer gig game mastering for Level Up Gaming League at Youth Empowerment Support Services here in Edmonton. The 3 hour long sessions at the shelter gather at-risk youth with staff and volunteers to roll dice, proclaim improvised epic poetry, and save worlds. If they’re lucky. The game table is a place for youth to relax, take a break from daily stresses, and knock around a few goblins. But it’s also a place they can experiment with identity, take big social risks in a safe environment, and build their communication skills.

Even being a cheerleader for gaming for social growth (as I am), I did not expect my hours crowded with friends around a kitchen table to be so useful in business! For the benefit of nerds who would be entrepreneurs, and entrepreneurs who could use a little creative mojo, I am pleased to present 5 Things Dungeons and Dragons Taught Me About Starting a Business.

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1. You must gather your party before venturing forth.

The Barbarian is a force of nature. His axe is enchanted obsidian, chipped from the summit of Mount Ignus. His bare skin is merely bronzed by the searing sun and so thick it turns blades with nary a mark. His rage is a cataclysm that sunders shorelines into the sea. He faces the hordes. He blinks. They tremble.

But one itsy bitsy mind control spell… and the force of nature belongs to someone else. Unlike the myriad single player video games where the character you control is a God, up to every challenge. Dungeons and Dragons is a team game. Every character has weaknesses and needs a team to back them up. 

And so it is in business. I’ve spent twelve years in the window cleaning and homes services industry. I thought I’d seen every part of the business, from field work, to sales, to management. The first day I sat looking at a business plan template though, I felt underprepared. Luckily, that wasn’t a problem. It takes a party to complete a quest. I didn’t quite hang out a recruitment poster at my local tavern, but I did start asking around. Friends and businesspeople I’ve come to know were delighted to share their favourite lawyers and accountants, SEO people and more. 

Some businesses clearly require more talent from the word go. No one person is going to muscle up a restaurant and fill all the roles by themselves. Maaaaybe a food truck. Some of my services could be offered solo. Lots of window cleaners work alone. But, even without staff, a party of mentors and professional advisors has built my confidence and guided me through many paperwork labyrinths. 

2. Guessing doesn’t go very far. Sometimes you have to open the door to find out what’s behind it.

How many hours have I argued about the best course of action concerning an unknowable something on the other side of that door. Or through that portal. Or possessing Bryan. It’s natural to be precious, to want to control all the variables. It’s all part of wanting to win. Intolerance of risk is a problem though. At the game table it’s a drag on pacing. Everyone’s huddled around the chest wondering if it’s full of poison gas, and instead of opening and finding out, they talk. Hesitant players can talk for agonizing hours.

If I’m totally intolerant of risk in business, guess what? I’m not going to start my business. This hits most true for me when I’m cold calling. I have the property manager’s number. I just need to call her and ask to be added to her bidding list. But what if she is full of poison gas? What if she… what? Makes fun of me? I’m not downplaying the validity of social fears. I have them. But when I write it all down like this, the danger of losing my investment money seems worse than a no on the other end of a phone. After all, coming up with new investment money is harder even than rolling up a new character. 

3. Pay Attention to the Fine Print

Character sheets and notes to show you how many forms I've filled out for fun.
I’ve got lots of practice at paperwork.

How many devilish bargains have you made? I of course have made zero. Sir Nielken Foehammer, brother of the Phoenix Order, and Lord of Red Wyrm’s Keep, on the other hand, made one. In the end, his safe passage through the Howling Underway, was not fair trade for perpetual banishment from his lands and holdings. It turned out some of those clauses had more than one interpretation. 

And while the typical CRA Agent is not so evil as Gelixan the Initiator, we’d do well to be wary. An awful lot more time has been put into drafting up tax and employment law than your average game master puts into drafting an infernal contract. The former are more byzantine and more confusing.

Especially starting out, I find temptations abound to ‘seal it with a handshake,’ and keep everything friendly and simple. It isn’t that I’m paranoid that people are out to screw me. Though that certainly would be a Dungeons and Dragons appropriate lesson. It’s that misunderstandings happen easily. And, as a small business, your employees have Employment Standards on their sides, and most other companies you’re working with are bigger than you. They can outspend you to have agreements interpreted their way. I don’t see contracts as a way of getting one over on someone. By paying attention to the fine print agreements can be made with confidence. I want the business relationships I enter into to bring value to both parties for a long time. Oh how happy Nielken and Gelixan could have been had they approached things differently.

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4. Change the Parameters of the Encounter

“So you told the Unbreakables we’d make a distraction for them this morning. We’d raise a ruckus by the oasis so they could get in under the merchant’s wagon and get whatever they’re looking for. Is that right?”


“And they said, having gotten away with it, they’ll light the baggage train on fire tonight? That’ll be when we break into the royal’s wagon?”

“That’s their plan.”

“And you trust them?”

“Nope. I’m going to point them out to the guards when they try the merchant wagon. That should be plenty distraction for us.”

The winningest feature of playing at the table with friends, is having a live game master. There isn’t a video game yet that can give you options to try every ridiculous idea you might come up with. But a game master (poor fool) has to roll with whatever you bring to the table.

He might have had a rollicking chase scene planned, but when your wizard polymorphed bad guys’ horses into slugs, the parameters changed. 

Real life is like that! Not the polymorphing so much, but the infinite possibilities. I can’t tell you how exciting it is to turn a conversation with a competitor into a talk about subcontracting for them in a service area they don’t have training in. When an encounter seems like nothing can be gained from it, a little creativity can turn it into opportunity. 

5. Sometimes You’ll Lose. It’s All Part of the Story.

Earlier I referred to Dungeons and Dragons as “the infinite game.” It’s so called because you can’t really win it. You can win an encounter, or complete a quest. But, there isn’t a credit roll when you’re all finished. The point of it is the experience of playing. When your characters become semi-deities, and there isn’t anything exciting or new for them to do, you put their character sheet to the side. And if you love the game, you roll up a crook toothed farmer with a crush on the King’s whipping boy, and a habit of cursing in polite company. 

Sometimes you lose though, you muck up an encounter and fail to achieve what you set out to. No save point. No reset. Sometimes your character gets killed, and you have to say goodbye to their story before their potential was realized. But, if you hold on too tightly to what you’ve lost, you’ll miss out on the magic that happens next. You’ll miss out on the resonances that loss has on the story: the lessons learned, the tributes made, and the new purposes discovered.

I think a lot about the fail-state of my business. What if the customers don’t come? What if I get injured? What if COVID-19 completely tanks the economy and nobody gives two shakes anymore if their windows and siding are clean? I might lose my house over it. My daughter would likely need to go into full time care, something we’ve avoided as long as we’ve been blessed enough to be able. And I don’t want those things to happen.

I believe to achieve what I want, to build security for those I love, and to delight those I serve, I’ll have to face a lot of losses along the way. There will be failed bids, poorly performing investments, and misunderstandings between myself and customers/employees/suppliers. I’ll have lots of face to face time with my own shortcomings and I endeavour to have the strength to face them. Some days I won’t. Some days everything will be out of control. The dice will roll critical fails.

I can’t control the dice. I can only control my responses to them. Taking the next step, and making the best decisions I can is the best I can do. That, and putting the bad dice in jail.

May you always roll 20s.

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